Weekly Review 5

Weekly Review 5 - d. Thiolate (NaSR) e. Amines 5) Robinson...

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Review 5 Weekly Review Lecture Chem S 20ab Reactions you learned this week (add to your chart): 1) Amino acids a. Strecker synthesis b. Peptide bond formation i. Solution phase ii. Merrifield resin c. Protecting and deprotecting i. Boc ii. Tert-butyl ester hydrolysis (originally learned last week) 2) Reactions involving enols/enolates a. Deuteration at alpha position b. Halide addition at alpha position i. Base catalyzed - Leading to cleavage of CX 3 H for methyl ketones ii. Acid catalyzed c. Aldol addition d. Aldol condensation e. Claisen condensation f. Alkylation of -dicarbonyl enolates g. Enolate formation using LDA i. Kinetic conditions ii. Thermodynamic conditions h. “Reformatsky” enolate formation i. Alkylation at alpha position using a lithium or zinc enolate j. Lithium enolates attacking epoxides 3) Decarboxylation of beta-keto acids 4) Conjugate additions a. Lithium dialkyl cuprates b. Michael addition c. NaCN (in alcohol solvent)
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Unformatted text preview: d. Thiolate (NaSR) e. Amines 5) Robinson annulation = Michael addition + aldol condensation Part I: Anomeric Effect 1. Explain the following observation by a frontier molecular orbital (FMO) argument. Be sure to label the relevant donor-acceptor interactions and provide a clear diagram showing the interacting orbitals. The infrared stretching frequency for the C=N bond for compound 1 , below, is greater than the stretching frequency for the C=N bond in compound 2 . Review 5 Weekly Review Lecture Chem S 20ab Part II: Mechanisms 2. Provide a curved arrow mechanism for each reaction. a. b. Part III: Synthesis 3. Provide a complete synthetic route from the given starting material to the indicated product. Unless otherwise indicated, you may use any organic or inorganic reagents. a. b. c. Review 5 Weekly Review Lecture Chem S 20ab d. e. f. g. h. i....
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Weekly Review 5 - d. Thiolate (NaSR) e. Amines 5) Robinson...

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